DE1569773B1 - Pigment of the bis (tetrachloro-isoindolin-l-one-3-ylidenimino) -aryl series and process for its preparation - Google Patents

Description

In the series of strongly colored bis (tetrachloro-isoindolin- io
l-on-3-ylidenimino) -aryl compounds which cause the condensation of 2,2'-diamino-diphenyl with

Nowadays the properties required for pigments are the 4,5,6,7 substituted in the 3-position, red, orange and reddish yellow tetrachloroisoindolin-1-one occurs even in the cold, Shades before. For example, the 4,4'-di-, if necessary with heating, is the intimately mixed pigment having phenyl radical as a bridge member 15 components, particularly advantageous in the presence orange. However, strongly colored, green-inert ones, i.e. not taking part in the reaction, are very popular pungent yellow pigments. organic solvent.

It has now been found that a greenish tinge- if one goes from alkali salts (especially from Na-

yellow and strongly colored pigment of the bis (tetrachlorotrium salt) of 3,3-dialkoxy-4,5,6,7-tetrachloro-isorndoisoindolin-1-one-3-ylidenimino) aryl series obtained when 20 lin-1-ones or from 3-imino-, 3-thio- or 3,3-bismane 1 mole of 2,2'-diaminodiphenyl with 2 moles of ernes tert. amino-4,5,6,7-tetrachloro-isoindolin-l-ones from, see above 4,5,6,7-tetrachloro-isoindolin-1-one, which is used in 3-places advantageously with water miscible Development contains easily interchangeable substituents that organic solvents, e.g. B. low molecular weight alinach Type and number of two bonds claim and phatic alcohols, such as low molecular weight alkanols, are more implementable than the doubly bound 25, for example, methanol or ethanol, low mol-

Oxygen, to a compound of the formula

Cl

Cl

kular cyclic ethers, such as dioxane, low molecular weight aliphatic ketones, such as acetones, or low molecular weight Fatty acids, ζ. B. acetic acid. The condensation takes place here even at relatively low temperatures. It is advantageous to work in the presence of base-binding agents; as such are for example low molecular weight fatty acids, which then also serve as solvents, especially acetic acid, to mention.

When using 3,3-dihalo-4,5,6,7-tetrachloroisoindolin-1-ones preference is given to organic solvents free of hydroxyl groups, such as hydrocarbons, z. B. aromatic, such as benzene, toluene, xylenes, tetrahydronaphthalene or diphenyl, or cycloaliphatic, z. B. cyclohexane, then also halogenated hydrocarbons, such as aliphatic, z. B. Carbon tetrachloride or tetrachlorethylene, or aromatic ones, such as chlorobenzene or di- and trichlorobenzenes, also aromatic nitro hydrocarbons, such as nitrobene

condensed.

The 4,5,6,7-Tetra ^ which can be used as starting materials contain movable substituents in the 3-position chloro-isoindolin-1-one, for example, two halogen,

in particular chlorine atoms, two secondary amino 45 zol, ethers, namely aliphatic, such as dibutyl ether,

groups, especially piperidino or morpholino aromatic, such as diphenyl ether, or low molar

groups, or two alkoxy, ζ. B. methoxy or kulare cyclic ethers, such as dioxane, also ketones,

Ethoxy groups, an imino or a thio group. like acetone, or esters, namely esters of low

They preferably contain two methmolecular fatty acids with low molecular weight alkali in the 3-position

oxy groups. 5 ° noles.

These starting materials are known; two halogen The new pigment falls immediately after its

Compounds containing atoms in the 3-position are formed from the reaction medium. It is for

is obtained, for example, by the action of certain purposes as a crude pigment that can be used directly;

Halogenating agents, such as phosphorus pentachloride, but it can also be done by methods known per se,

on tetrachlorophthalic acid imide. The 55 produced in this way, for example, by crystallization or extraction

3.3 -. Dihalogen - 4,5,6,7 - tetrachloro - isoindolin - 1 - one with organic solvents or by grinding

can be converted into the grinding aids, which can be removed again afterwards, by reacting with ammonia,

3-imino or with secondary amines or with e.g. salts, in its properties, especially

Alkanols in the 3,3-bis-tert. amino or 3,3-dialk plus purity, shape and opacity, even more

Convert oxy-4,5,6,7-tetrachloroisoindolin-1-one. 60 to be improved.

4,5,6,7-Tetrachlor-isoindolin-l-one with two alkoxy- The new pigment of the bis-tetrachlor-isoindoline-

groups in the 3-position can also be obtained by um-1-one series for pigmenting polymeric materials

Settlement of a 3,4,5,6-tetrachloro-2-cyano-benzoic acid organic material suitable, for. B. in printing inks

esters, ζ. B. the methyl ester, with the desired for the graphic industry, in paints

Alkanol in the presence of alkali or alkaline earth 65 oily bases, such as linseed oil paints, or on

metals, alkali or alkaline earth oxides or -hy- aqueous bases, such as in emulsion paints, or

Produce droxyden, which in the implementation with the in varnishes of various types, such as in nitro or

Alcohols form the corresponding alcoholates. Stoving enamels, in the latter case e.g. B. such on

Alkyd resin base. It can also be used for spin dyeing of viscose or cellulose acetate, for pigmenting plastics such as polyethylene, Polystyrene, polyvinyl chloride, which the latter can also contain plasticizers, of cellulose esters, of curable resins, or for pigmenting rubber and for coloring paper pulp or Use for coating webs, e.g. in the production of laminate paper.

The new pigment results in pure, bright greenish-yellow pigmentations in these materials. The pigment according to the invention is distinguished from known pigments of a similar constitution characterized in that it has the much sought-after, greenish yellow hue with an unexpectedly high color strength remarkably good fastness properties, in particular high light fastness, very good migration fastness in structures Made of plasticized polyvinyl chloride, excellent overcoating, rubbing and dry cleaning fastness and good heat resistance combined.

Compared to known compounds of this class of substances which are comparable in color and which are unsubstituted Having m-phenylene radical as a bridge link, the new pigment stands out, despite the higher Molecular weight, characterized by greater color strength.

The following examples illustrate the invention. The temperatures are in degrees Celsius indicated and the percentages in percentages by weight.

example 1

35

40

45

16.5 g of S ^ -dimethoxy- ^ oJ-tetrachloro-isoindoHn-1-one and 4.6 g of 2,2'-diaminodiphenyl are refluxed in 200 ecm of glacial acetic acid for 2 hours heated. The pigment formed is filtered off while hot and washed with ethanol. You get after drying, 17 g of pigment of the above formula, which can be used directly as Greenish yellow pigment of excellent fastness properties can be used.

Is used instead of 16.5 g of 3,3-dimethoxy-4,5,6,7-tetrachloro-isoindolin-1-one 14.2 g of 3-imino-4,5,6,7-tetrachloro-isoindolin-1-one or 22.1 g of 3,3-dimorpholino-4,5,6,7-tetrachloro-isoindolin-1-one and if the rest of the procedure is as indicated in the example, the same pigment is obtained in a similarly good yield.

0.6 g of the pigment prepared according to paragraph 1 of this example are mixed with 67 g of polyvinyl chloride, 33 g of dioctyl phthalate, 2 g of dibutyltin dilaurate and 2 g of titanium dioxide mixed together for 10 to 15 minutes rolled at 140 °. Greenish-tinged yellow polyvinyl chloride films produced in this way are resistant to migration, heat and dyed lightfast.

10 g of titanium dioxide (rutile) and 2 g of the pigment prepared in accordance with paragraph 1 of this example are mixed with 88 g of a mixture of 26.4 g coconut alkyd resin, 24.0 g melamine-formaldehyde resin (50% solids content), 8.8 g of ethylene glycol monomethyl ether and 28.8 g of xylene in a ball mill for 48 hours ground.

If this lacquer is sprayed onto an aluminum foil and after 30 minutes pre-drying at Baked at room temperature for 30 minutes at 120 °, the result is a coating that is characterized by a pure, greenish yellow hue. The paintwork is very well painted over and lightfast.

Example 2

To a solution of 17 g of 3,3,4,5,6,7-hexachloroisoindolin-1-one in 200 ml of 1,2-dichlorobenzene, a solution of 4.6 g of 2,2'-diaminodiphenyl in 100 ecm 1 ^ -Dichlorobenzene added. A yellow precipitate forms immediately. The suspension will heated to 160 to 170 ° and kept at this temperature with stirring for 1 hour. The insoluble The pigment is filtered off while hot and washed with ethanol and water. One receives after drying 13.9 g of the pigment described in Example 1.

Example 3

31.4 g are added to a sodium methylate solution (obtained from 2.7 g of sodium and 120 ecm of methanol) 3,4,5,6-tetrachloro-2-cyanobenzoic acid methyl ester. This produces the sodium salt of 3,3-dimethoxy - 4,5,6,7 - tetrachloro - isoindolin - 1 - one. After 30 minutes, 9.2 g of 2,2'-diamino-diphenyl are added to the solution formed entered and then the mixture was stirred for 10 hours at room temperature, whereby the yellow sodium salt of the dye separates. The reaction mixture is acidified with 40 ecm of glacial acetic acid and heated to reflux temperature for 2 hours. The insoluble pigment is filtered off while hot and washed with ethanol and acetone. After drying, 36 g of that described in Example 1 are obtained Pigments, which in this form can be used directly as a pigment with excellent fastness properties can.

To further improve its color strength, 15 g of crude pigment and 30 g of anhydrous calcium chloride are used in a 1-1 vibratory mill containing 3.5 kg of steel balls with a diameter of 1.5 cm. After 1 hour of vibration, the grist will turn off the vibration mill removed and the calcium chloride dissolved out with water. The dried pigment is now characterized by high color strength and transparency.

In order to obtain a pigment with constant color strength and good hiding power, 10 g Salt-ground pigment heated to reflux temperature with 100 ecm of chlorobenzene for 2 hours. The pigment is then filtered off while hot and dried.

For the production of a color paste for graphic purposes, 2 g of the according to paragraph 2 of this example produced pigments with 36 g of alumina hydrate, 60 g of linseed oil varnish of medium viscosity and 0.2 g of cobalt linoleate mixed and rubbed on the three-roll mill. The greenish yellow ones produced with this color paste Prints are strong, pure and extremely lightfast.

Claims (3)

i 569 claims: V. 1. Pigment the bis (tetrachloro-isoindolin-l-one-3-ylidenimino) -arylreihe _of: Formula ίο 2. Process for the production of a pigment of the bis (tetrachloro-isoindonii-l-on-3-ylideniniiao) -aryl series according to claim 1, characterized in that 1 mol of 2,2'-diaminodiphenyl with 2 moles of a 4,5,6,7-tetrachloroisoindolin-l-one, which contains easily exchangeable substituents in the 3-position, the type and number of which are two Tighten bonds and are more capable of action than the doubly bonded oxygen, to one Compound of the formula .....; Cl Cl condensed. 3. The method according to claim 2, characterized in that 1 mole of 2,2'-diaminodiphenyl with 2 mol a ^ -dimethoxy-iS.öJ-tetrachloro-isoindolin-1-one condensed. -., ..